Reacción #5958

Ecuación de reacción

Compound ( f )

N-[4-(2-Carbomethoxyphenyl)benzyl]phthalimide

Hydrazine hydrate

→

pale yellow oil

Rendimiento 66.3%

4-(2-Carbomethoxyphenyl)benzylamine

Rendimiento 66.3%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawith warming
2. 2
   TemperaturaThe solution is heated
3. 3
   Temperaturato reflux for 10 minutes
4. 4
   Filtraciónfiltered
5. 5
   LavadoThe precipitate is washed with excess hot ethanol

Procedimiento

Compound (f) of Example 6 (3.85 g, 0.01 mole) is dissolved in 100 mL of absolute ethanol with warming. Hydrazine hydrate (7.5 mL) is added at once. The solution is heated to reflux for 10 minutes and the reaction mixture sets up. The mixture is cooled to room temperature and filtered. The precipitate is washed with excess hot ethanol. The ethanol fraction is rotovapped to a pale yellow oil. Chromatography on silica gel using methylene chloride/25% methanol as the mobile phase yields 1.6 g (66%) of a pale yellow oil. 1H NMR (CDCl3) 7.83 (1H, d, J=7 Hz); 7.6-7.2 (7H, m); 3.92 (2H, s); 3.66 (3H, s); 2.16 (2H, bs). Mass Spec. (DCl) m/z 242 (M+H). Analysis--calc'd for C15H15NO2.H2O: C, 71.97; H, 6.44; N, 5.60; found: C, 71.60; H, 6.27; N, 5.70.

Fuente